Naples has always had a reputation for luxury, but nothing quite prepares you for what's sitting at the top of the market right now. The city consistently ranks among the wealthiest zip codes in the country — and one look at these listings tells you exactly why. We're talking private docks, resort-style pools, and finishes that belong in an architectural magazine. I went down a rabbit hole pulling together the five most expensive homes currently for sale in Naples — and honestly, I'm not sorry about it. Here's what $40M+ buys you in Southwest Florida.
P.S. - Let me know if you have any questions or would like to know how old the water heater is on these.
#1 - 100 Bay Road, Naples, FL 34102
$271,000,000
Listed by Gulf Coast International Properties - Tim Savage
There is a reason why this property has gained national exposure. Gordon Pointe is a one-of-a-kind piece of land spanning 9.17 acres and 722' of gorgeous, white sand beach on the Gulf of America. There are three homes on the property as well but I'm guessing the buyer will be building his or her own dream home.
Listing agent Tim Savage makes a great point in that the property is a true peninsula. That provides both the wide open views of the Gulf of America but also a safe harbor on the bay side of the property.
We've all cruised past this gorgeous property before on the Naples Princess but only now do you have the chance to submit an offer!
#2 - 20 14th Ave South, Naples, FL 34102
$89,000,000
Listed by Gulf Coast International Properties - Tim Savage, PA
This incredible 2.94 acre parcel of land is for sale for lot value and sits just a short stroll away from the Naples Pier to the north and 3rd Street South a little bit inland. Tim Savage notes that this is "the only remaining entire city block on the beach."
#3 - 1857 Galleon Drive, Naples, FL 34102
$59,995,000
Listed by William Raveis Real Estate - Rex Miller, PA
This 2026 build by VIV Homes and Kukk Architecture is breathtaking. This home sits on nearly a full acre on Galleon Drive in prestigious Port Royal. With incredibly close Gulf access and no bridges, your yacht is just a quick drive away from the open water.
Inside 1857 Galleon you will find 13,000 square feet under air with 6 bedrooms, a den and an exercise room. There are 7 full baths and 3 half and a five-car garage.
I do have some bad news though--this home is not expected to be complete until December 2026. If you were picking up the phone to contact me, you may want to hold off just a bit.
#4 - 1611 Gulf Shore Blvd N, Penthouse 5, Naples, FL 34102
$50,000,000
Listed by Ronto Realty - Van Osborne
In the third spot today, we travel to the Gulf-front, nearly 10,000 square foot penthouse in the brand new Rosewood Residences Naples. Located in Coquina Sands on Miracle Mile, this condo for sale is nearly ready occupancy. Will it be yours?
#5 - 3220 Rum Row, Naples, FL 34102
$44,000,000
Listed by London Bay Realty Inc. - Toby Cloutier
Full disclosure. I'm saving up for this one.
This Port Royal masterpiece features 160 feet of waterfront and the western exposure gives you our beautiful sunsets nightly. Inside you'll find the 6 bedrooms you need (as you'll soon have lots of guests), a den, club room and three laundry rooms.
Care to work with The Listing Naples Group and Chris Farrugia?
I had a little fun with this post but in all seriousness, I would love to help you purchase your next home. Maybe it won't be $50,000,000 like the fourth property and maybe closer to $300,000. That's fine by me! Let's start seeing what options are out there.
Please reach out and let's have a no-obligation discussion on your specific real estate needs. I'd love to answer any questions you may have.
I can be reached at:
☎️ (239) 248-8171 Call/Text
